3-[1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-N-[4-(4'-methyl-[2,2']bipyridinyl-4-yl)-butyl]-propionamide | 175355-10-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 3-[1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-N-[4-(4'-methyl-[2,2']bipyridinyl-4-yl)-butyl]-propionamide
• 英文别名: 3-[1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4-dioxopyrimidin-5-yl]-N-[4-[2-(4-methylpyridin-2-yl)pyridin-4-yl]butyl]propanamide
• CAS: 175355-10-9
• 化学式: C₂₇H₃₃N₅O₆
• 分子量: 523.589
• InChiKey: KBZRGEQZDVMTII-JBRSBNLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  154
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-[1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-N-[4-(4'-methyl-[2,2']bipyridinyl-4-yl)-butyl]-propionamide 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 10.0h， 生成 Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-{2-[4-(4'-methyl-[2,2']bipyridinyl-4-yl)-butylcarbamoyl]-ethyl}-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester
  参考文献：
  名称：

  Building Blocks for Ribozyme Mimics:  Conjugates of Terpyridine and Bipyridine with Nucleosides

  摘要：

  The incorporation of the 2,2':6',2 ''-terpyridyl (terpy) complex of Cu(II) into a deoxyoligonucleotide has led to a functional mimic of ribozymes. The resulting mimic can cleave target RNA in a sequence-directed manner by a hydrolytic mechanism. Here we describe the synthesis and characterization of four modified nucleoside phosphoramidite reagents (7, 10, 14, and 18) that contain pendant 2,2'-bipyridine or terpy ligands. The ligands are attached either to the nucleobase (7, 10) or to the sugar (14, 18). Nucleobase modification was carried out at the C-5 position of 2'-deoxyuridine (dU). One route to sugar modification was performed by synthesis of 18, a 1'-functionalized analog of dU based on 1-[3-deoxy-beta-D-psicofuranosyl]uracil. Another route to sugar functionaliztion resulted in 14, a 2'-O-alkyl derivative of adenosine. These modified nucleosides are building blocks for ribozyme mimics. They are designed to deliver hydrolytically active metal complexes across either the major groove (7, 10) or the minor groove (14, 18) of an RNA/DNA duplex.

  DOI：

  10.1021/jo9518213
• 作为产物：
  描述：

  5-(2-carbethoxyethyl)-2'-deoxyuridine 、 4-(4-aminobutyl)-4'-methyl-2,2'-bipyriridine 在 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 以82%的产率得到3-[1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-N-[4-(4'-methyl-[2,2']bipyridinyl-4-yl)-butyl]-propionamide
  参考文献：
  名称：

  Building Blocks for Ribozyme Mimics:  Conjugates of Terpyridine and Bipyridine with Nucleosides

  摘要：

  The incorporation of the 2,2':6',2 ''-terpyridyl (terpy) complex of Cu(II) into a deoxyoligonucleotide has led to a functional mimic of ribozymes. The resulting mimic can cleave target RNA in a sequence-directed manner by a hydrolytic mechanism. Here we describe the synthesis and characterization of four modified nucleoside phosphoramidite reagents (7, 10, 14, and 18) that contain pendant 2,2'-bipyridine or terpy ligands. The ligands are attached either to the nucleobase (7, 10) or to the sugar (14, 18). Nucleobase modification was carried out at the C-5 position of 2'-deoxyuridine (dU). One route to sugar modification was performed by synthesis of 18, a 1'-functionalized analog of dU based on 1-[3-deoxy-beta-D-psicofuranosyl]uracil. Another route to sugar functionaliztion resulted in 14, a 2'-O-alkyl derivative of adenosine. These modified nucleosides are building blocks for ribozyme mimics. They are designed to deliver hydrolytically active metal complexes across either the major groove (7, 10) or the minor groove (14, 18) of an RNA/DNA duplex.

  DOI：

  10.1021/jo9518213

文献信息

• Building Blocks for Ribozyme Mimics:  Conjugates of Terpyridine and Bipyridine with Nucleosides
  作者：James K. Bashkin、Jin Xie、Andrew T. Daniher、UmaShanker Sampath、Jeffrey L.-F. Kao

  DOI：10.1021/jo9518213

  日期：1996.1.1

  The incorporation of the 2,2':6',2 ''-terpyridyl (terpy) complex of Cu(II) into a deoxyoligonucleotide has led to a functional mimic of ribozymes. The resulting mimic can cleave target RNA in a sequence-directed manner by a hydrolytic mechanism. Here we describe the synthesis and characterization of four modified nucleoside phosphoramidite reagents (7, 10, 14, and 18) that contain pendant 2,2'-bipyridine or terpy ligands. The ligands are attached either to the nucleobase (7, 10) or to the sugar (14, 18). Nucleobase modification was carried out at the C-5 position of 2'-deoxyuridine (dU). One route to sugar modification was performed by synthesis of 18, a 1'-functionalized analog of dU based on 1-[3-deoxy-beta-D-psicofuranosyl]uracil. Another route to sugar functionaliztion resulted in 14, a 2'-O-alkyl derivative of adenosine. These modified nucleosides are building blocks for ribozyme mimics. They are designed to deliver hydrolytically active metal complexes across either the major groove (7, 10) or the minor groove (14, 18) of an RNA/DNA duplex.